Curable fiberglass binder

ABSTRACT

A curable formaldehyde-free binding composition for use with fiberglass is provided. Such curable composition comprises an addition product of an amine and a reactant to form an amino-amide intermediate. To the amino-amide is added an aldehyde or ketone to form the curable binder composition. The composition when applied to fiberglass is cured to form a water-insoluble binder which exhibits good adhesion to glass. In a preferred embodiment the fiberglass is in the form of building insulation. In other embodiments the product is a microglass-based substrate for use in a printed circuit board, battery separator, filter stock, or reinforcement scrim.

CROSS-REFERENCE TO RELATED APPLICATION

This application is a division of prior pending U.S. application Ser.No. 12/539,263 filed Aug. 11, 2009. The entire contents of theabove-identified application is herein incorporated by reference for allpurposes.

BACKGROUND

The subject invention pertains to an improved binding composition foruse with fiberglass. More specifically, the invention pertains to animproved curable composition comprising an addition product of an amineand a reactant in the form of a amino-amide intermediate. An aldehyde orketone is added to the amino-amide to form a composition which uponcuring is capable of forming a water-insoluble polymer composition whichdisplays good adhesion to glass. Once applied to the fiberglass, thebinding composition is cured. The binder of the present invention isuseful as a fully acceptable replacement for formaldehyde-based bindersin non-woven fiberglass products, and actually provides a binderexhibiting improved physical properties.

Fiberglass binders have a variety of uses ranging from stiffeningapplications where the binder is applied to woven or non-wovenfiberglass sheet goods and cured, producing a stiffer product;thermo-forming applications wherein the binder resin is applied to asheet or lofty fibrous product, following which it is dried andoptionally B-staged to form an intermediate but yet curable product; andto fully cured systems such as building insulation.

Fibrous glass insulation products generally comprise matted glass fibersbonded together by a cured thermoset polymeric material. Molten streamsof glass are drawn into fibers of random lengths and blown into aforming chamber where they are randomly deposited as a mat onto atraveling conveyor. The fibers, while in transit in the forming chamberand while still hot from the drawing operation, are sprayed with anaqueous binder. A phenol-formaldehyde binder has been used throughoutthe fibrous glass insulation industry. The residual heat from the glassfibers and the flow of air through the fibrous mat during the formingoperation are generally sufficient to volatilize water from the binder,thereby leaving the remaining components of the binder on the fibers asa viscous or semi-viscous high solid liquid. The coated fibrous mat istransferred to a curing oven where heated air, for example, is blownthrough the mat to cure the binder and rigidly bond the glass fiberstogether.

Fiberglass binders used in the present sense should not be confused withmatrix resins which are an entirely different and non-analogous field ofart. While sometimes termed “binders”, matrix resins act to fill theentire interstitial space between fibers, resulting in a dense, fiberreinforced product where the matrix must translate the fiber strengthproperties to the composite, whereas “binder resins” as used herein arenot space-filling, but rather coat only the fibers, and particularly thejunctions of fibers. Fiberglass binders also cannot be equated withpaper or wood product “binders” where the adhesive properties aretailored to the chemical nature of the cellulosic substrates. Many suchresins are not suitable for use as fiberglass binders. One skilled inthe art of fiberglass binders would not look to cellulosic binders tosolve any of the known problems associated with fiberglass binders.

Binders useful in fiberglass insulation products generally require a lowviscosity in the uncured state, yet possess characteristics so as toform a rigid thermoset polymeric binder for the glass fibers when cured.A low binder viscosity in the uncured state is required to allow the matto be sized correctly. Also, viscous binders commonly tend to be tackyor sticky and hence they lead to the accumulation of fiber on theforming chamber walls. This accumulated fiber may later fall onto themat causing dense areas and product problems. A binder which forms arigid matrix when cured is required so that a finished fiberglassthermal insulation product, when compressed for packaging and shipping,will recover to its as-made vertical dimension when installed in abuilding.

From among the many thermosetting polymers, numerous candidates forsuitable thermosetting fiberglass binder resins exist. However,binder-coated fiberglass products are often of the commodity type, andthus cost becomes a driving factor, generally ruling out resins such asthermosetting polyurethanes, epoxies, and others. Due to their excellentcost/performance ratio, the resins of choice in the past have beenphenol-formaldehyde resins. Phenol-formaldehyde resins can beeconomically produced, and can be extended with urea prior to use as abinder in many applications. Such urea-extended phenol-formaldehydebinders have been the mainstay of the fiberglass insulation industry foryears, for example.

Over the past several decades however, minimization of volatile organiccompound emissions (VOCs) and hazardous air pollutants (HAPS) both onthe part of the industry desiring to provide a cleaner environment, aswell as by Federal regulation, has led to extensive investigations intonot only reducing emissions from the current formaldehyde-based binders,but also into candidate replacement binders. For example, subtle changesin the ratios of phenol to formaldehyde in the preparation of the basicphenol-formaldehyde resole resins, changes in catalysts, and addition ofdifferent and multiple formaldehyde scavengers, has resulted inconsiderable improvement in emissions from phenol-formaldehyde bindersas compared with the binders previously used. However, with increasinglystringent Federal regulations, more and more attention has been paid toalternative binder systems which are free from formaldehyde.

One such candidate binder system employs polymers of acrylic acid as afirst component, and a polyol such as triethanolamine, glycerine, or amodestly oxyalkylated glycerin as a curing or “crosslinking” component.The preparation and properties of such poly(acrylic acid)-based binders,including information relative to the VOC emissions, and a comparison ofbinder properties versus urea-formaldehyde binders is presented in“Formaldehyde-Free Crosslinking Binders For Non-Wovens,” Charles T.Arkins et al., TAPPI Journal, Vol. 78, No. 11, pages 161-168, November1995. The binders disclosed by the Arkins article, appear to beB-stageable as well as being able to provide physical properties similarto those of urea/formaldehyde resins.

U.S. Pat. No. 5,340,868 discloses fiberglass insulation products curedwith a combination of a polycarboxy polymer, a-hydroxyalkylamide, and atleast one trifunctional monomeric carboxylic acid such as citric acid.The specific polycarboxy polymers disclosed are poly(acrylic acid)polymers. See also, U.S. Pat. No. 5,143,582.

U.S. Pat. No. 5,318,990 discloses a fibrous glass binder which comprisesa polycarboxy polymer, a monomeric trihydric alcohol and a catalystcomprising an alkali metal salt of a phosphorous-containing organicacid.

U.S. 2007/0142596 discloses binders comprised of a mixture of Maillardreactants. The reactants comprise a monosaccharide and an ammonium saltof a polycarboxylic acid.

Published European Patent Application EP 0 583 086 A1 appears to providedetails of polyacrylic acid binders whose cure is catalyzed by aphosphorus-containing catalyst system as discussed in the Arkins articlepreviously cited. Higher molecular weight poly(acrylic acids) are statedto provide polymers exhibiting more complete cure. See also U.S. Pat.Nos. 5,661,213; 5,427,587; 6,136,916; and 6,221,973.

Some polycarboxylic polymers have been found useful for makingfiberglass insulation products. Problems of clumping or sticking of theglass fibers to the inside of the forming chambers during theprocessing, as well as providing a final product that exhibits therecovery and rigidity necessary to provide a commercially acceptablefiberglass insulation product, have been overcome. See, for example,U.S. Pat. No. 6,331,350. The thermosetting acrylic resins have beenfound to be more hydrophilic than the traditional phenolic binders,however. This hydrophilicity can result in fiberglass insulation that ismore prone to absorb liquid water, thereby possibly compromising theintegrity of the product. Also, the thermosetting acrylic resins nowbeing used as binding agents for fiberglass have been found to not reactas effectively with silane coupling agents of the type traditionallyused by the industry increasing product cost. The addition of siliconeas a hydrophobing agent results in problems when abatement devices areused that are based on incineration as well as additional cost. Also,the presence of silicone in the manufacturing process can interfere withthe adhesion of certain facing substrates to the finished fiberglassmaterial. Overcoming these problems will help to better utilizepolycarboxylic polymers in fiberglass binders.

Accordingly, in one aspect the present invention provides a novel,non-phenol-formaldehyde binder.

Another aspect of the invention provides a novel fiberglass binder whichprovides advantageous flow properties, the possibility of lower binderusage, the possibility of overall lower energy consumption, eliminationof interference in the process by a silicone, and improved overalleconomics.

Still another aspect of the present invention is to provide a binder forfiberglass having improved economics, while also enjoying improvedphysical properties. In addition, the present invention increases thesustainable portion of the binder and reduces the dependency on a fossilbased source for the resin.

These and other aspects of the present invention will become apparent tothe skilled artisan upon a review of the following description and theclaims appended hereto.

SUMMARY OF THE INVENTION

A curable composition for use in the binding of fiberglass is providedcomprising an addition product of an amine and a saturated orunsaturated reactant in the form of an amino-amide intermediate. To thisintermediate is added an aldehyde or ketone, preferably a reducingsugar, to form a curable binder composition. This composition uponcuring is capable of forming a water-insoluble polymer composition whichexhibits good adhesion to glass.

A process for binding fiberglass is provided comprising applying tofiberglass a coating of a composition comprising an addition product ofan amine and a saturated or unsaturated reactant in the form of anamino-amide intermediate, to which is added an aldehyde or ketone.Thereafter the composition is cured while present as a coating on thefiberglass to form a water-insoluble polymer composition which exhibitsgood adhesion to the fiberglass.

In one embodiment, the amino-amide intermediate is first heated tocreate an oligomer. The aldehyde or ketone is added to the oligomer.This composition is added to the fiberglass as a binder and cured.

In a preferred embodiment the resulting fiberglass product is buildinginsulation. A roofing membrane is also a useful application. In otherembodiments the fiberglass product is a microglass-based substrateuseful when forming a printed circuit board, battery separator, filterstock, or reinforcement scrim.

DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS

The novel fiberglass binder composition of the present invention is acurable composition comprising the reaction product of an amine and asaturated or unsaturated reactant to form an amino-amide intermediate.

In accordance with one embodiment of the invention, amine reactants areselected which are capable of undergoing conjugate addition to form therequisite amino-amide, which forms a water-insoluble polyimide uponcuring. In such an embodiment the amine is a di- or multi-functionalprimary or secondary amine. More preferably, the amine is a diaminehaving at least one primary amine group.

Example of amines include, but are not limited to, aliphatic,cycloaliphatic and aromatic amines. The amines may be linear orbranched. The amine functionalities may be di- or multifunctionalprimary or secondary amines. The amines can include otherfunctionalities and linkages such as alcohols, thiols, esters, amides,acids, ethers and others.

Representative amines that are suitable for use in such an embodimentinclude 1,2-diethylamine, 1,3-propanediamine, 1,4-butanediamine,1,5-pentanediamine, 1,6-hexanediamine, .alpha.,.alpha.′-diaminoxylene,diethylenetriamine, triethylenetetramine, tetraethylenepentamine, andmixtures of these. A preferred diamines for use in this embodiment ofthe invention are 1,4-butanediamine and 1,6-hexanediamine. Natural andsynthetic amino acids such as lysine, anginine, hestidine, etc. can alsobe used.

The curable amino-amide is formed through the selection of anunsaturated or saturated reactant that is an anhydride, carboxylic acid,ester, and salts and mixtures of such reactants. Representativeunsaturated reactants are maleic acid, fumaric acid, maleic anhydride,mono- and di-esters of maleic acid and fumaric acid, and salts andmixtures of these. Ammonium salts of the unsaturated acids of theirmonoesters conveniently can be utilized. A preferred unsaturatedreactant is maleic anhydride. Representative saturated reactantsinclude, but are not limited to, succinic anhydride, succinic acid, monoand diesters of succinic acid, glutaric acid and anhydride, phthalicacid and anhydride, tetrahydro phthalic acid and anhydride, mono anddiesters of acid anhydrides and salts of the acids, and their monoesters. A preferred saturated reactant is phthalic anhydride ortetrahydro phthalic anhydride.

The amino-amide addition products can be readily formed by mixing thecomponents in an aqueous medium at room temperature. The resultingaddition products are either water-soluble, water-dispersible, or arepresent as an emulsion. To the solution of amino-amide, the carbonylfunctional materials can be added, especially an aldehyde or ketone. Dueto their higher reactivity, aldehydes are preferred to ketones. Thecomposition comprises the amino-amide and the aldehyde and/or ketone.Some reaction does take place within the composition between thecomponents. However, the reaction is completed during the curing step,followed by the cross-linking reaction of curing.

Examples of suitable aldehydes include, but are not limited to, mono-and multifunctional aldehydes including acetaldehyde, hydroxyacetaldehyde, butyraldehyde, acrolein, furfural, glyoxal,glyceraldehyde, glutaraldehyde, polyfurfural, polyacrolein, copolymersof acrolein and others. Reducing mono, di- and polysaccharides such asglucose, maltose, etc. can be used, with reducing monosaccharides suchas glucose being preferred.

Examples of ketones include, but are not limited to, acetone, acetylacetone, 1,3-dihydroxy acetone, benzyl, benzoin, fructose, etc.

The aldehydes and ketones react with the amino-amide intermediate, whichcontains an amic acid function, i.e., an amide linkage in the vicinityof a carboxylic acid. An amic acid function is more reactive than asimple carboxylic acid. The amount of aldehyde and/or ketone added isgenerally such that the molar ratio of carboxylic acid in theamino-amide to carbonyl or ketone is from 1:5 to 50:1. A ratio of 1:20to 20:1 is more preferred, with a ratio of 1:10 to 10:1 being mostpreferred.

One advantage is that the presence of all functional groups, i.e.,amine, amide and carboxylic acid, on the same molecule eliminates thepotential need for the addition of external crosslinkers or binders suchas polycarboxylic acids and/or polyvinyl alcohol. Such crosslinkers canbe added, however if desired.

In an embodiment, the amino-amide can be first oligomerized prior toadding the aldehyde or ketone. The amino-amide can be heated until anoligomer is obtained, e.g., a dimer, trimer or tetramer of theamino-amide intermediate. An example of suitable conditions for makingthe oligomer involves heating in the range of from 120-150° C. for up to5 hours.

Using the oligomerized product has been found to result in a more robustbinder product upon curing. This manifests itself in the strength of thebinder, and allows for better storage results, higher tensile strengthand rigidity, and better recovery for products made with the binder.

The composition when applied to the fiberglass optionally can includeadhesion prompters, oxygen scavengers, solvents, emulsifiers, pigments,fillers, anti-migration aids, coalescent aids, wetting agents, biocides,plasticizers, organosilanes, anti-foaming agents, colorants, waxes,suspending agents, anti-oxidants, crosslinking catalysts, secondarycrosslinkers, and combinations of these.

The fiberglass to which the composition according to the presentinvention is applied may take a variety of forms and in a preferredembodiment is building insulation. Roofing membranes is also a usefulapplication due to good characteristics. In other embodiments thefiberglass is a microglass-based substrate useful in applications suchas printed circuit boards, battery separators, filter stock, andreinforcement scrim.

The composition of the present invention can be applied to thefiberglass by a variety of techniques. In preferred embodiments theseinclude spraying, spin-curtain coating, and dipping-roll coating. Thecomposition can be applied to freshly-formed fiberglass, or to thefiberglass following collection. Water or other solvents can be removedby heating.

Thereafter the composition undergoes curing wherein a polymeric coatingis formed which exhibits good adhesion to glass. The polymericcomposition obtained upon curing is a combination of a polyamino-amideand a polyamino-imide. The polyimide is the primary product, but some ofthe amide in the intermediate is believed to not form the imide. Thus,some polyamino-amide is also present in the cured composition/binder.

Such curing can be conducted by heating. Elevated curing temperatures onthe order of 100 to 300° C. generally are acceptable. Satisfactorycuring results are achieved by heating in an air oven at 200° C. forapproximately 20 minutes.

The cured binder at the conclusion of the curing step commonly ispresent as a secure coating on the fiberglass in a concentration ofapproximately 0.5 to 50 percent by weight of the fiberglass, and mostpreferably in a concentration of approximately 1 to 10 percent by weightof the fiberglass.

The present invention provides a formaldehyde-free route to form asecurely bound formaldehyde-free fiberglass product. The bindercomposition of the present invention provides advantageous flowproperties, the elimination of required pH modifiers such as sulfuricacid and caustic, and improved overall economics and safety. The binderalso has the advantages of being stronger and offering lower amounts ofrelative volatile organic content during curing, which ensures a saferwork place and environment. The cure time of the binder is also seen tobe much faster and therefore does favor the economics, while reducingthe energy consumption during the curing process and lowering the carbonfootprint. The binder also contains a high level of sustainable rawmaterials further reducing the dependency on fossil based sources forthe resin. Also, due to the hydrophobic nature of the binder, the needfor a water repellant such as silicones is eliminated or greatlyreduced.

The following examples are presented to provide specific examples of thepresent invention. In each instance the thin glass plate substrate thatreceives the coating can be replaced by fiberglass. It should beunderstood, however, that the invention is not limited to the specificdetails set forth in the Examples.

Preparation of Intermediates—

To 116 g 1, 6 diaminohexane (HMDA) dissolved in 214 g water, 98 g maleicanhydride (MAn) was added slowly (molar ratio of 1:1) and the solutionwas stirred for 10 min. The intermediate was labeled HM.

To 116 g HMDA dissolved in 264 g water was added to 148 g phthalicanhydride. After the anhydride dissolved, the intermediate was labeledHP.

To 116 g HMDA dissolved in 268 g water was added 152 g tetrahydrophthalic anhydride. The solution was stirred until all anhydridedissolved. The intermediate was labeled HT.

These intermediates were utilized to make the following resins withglucose.

Example 1

To 42.8 g of solution of the HM intermediate anhydrous dextrose(alpha-D-glucose) and water were added. The mass of added water waschosen to be equal to that of the corresponding dextrose. The mass ofdextrose (and corresponding water) was 18 g, 36 g, 54 g, 72 g 90 g, 108,144, 180 g and 216 g. The various solutions were stirred at ambienttemperature for 10 mn. The solutions were applied as a thin film onglass and A1 panel, dried in an oven at 100° C. for 5 min and cured at200° C. for 20 min. Each of the solutions formed a cured brown polymerwhich was hard and insoluble in water and solvents, and showed anexcellent adhesion to glass.

Example 2

To 52.8 g of solution of the HP intermediate, anhydrous dextrose(alpha-D-glucose) and water were added. The mass of added water waschosen to be equal to that of the corresponding dextrose. The mass ofdextrose (and corresponding water) was 18 g, 36 g, 54 g, 72 g, 90 g,108, 144, 180 g and 216 g. The various solutions were stirred at ambienttemperature for 10 min. The solutions were applied as a thin film on aglass and A1 panel, dried in an oven at 100° C. for 5 min and cured at200° C. for 20 min. Each solution formed a cured brown polymer which washard and insoluble in water and solvents, and showed an excellentadhesion to glass.

Example 3

To 53.6 g of solution of the HT intermediate, anhydrous dextrose(alpha-D-glucose) and water were added. The mass of added water waschosen to be equal to that of corresponding dextrose. The mass ofdextrose (and corresponding water) was 18 g, 36 g, 54 g, 72 g, 90 g,108, 144, 180 g and 216 g. The various solutions were stirred at ambienttemperature for 10 min. The solutions were applied as a thin film onglass and A1 panel, dried in an oven at 100° C. for 5 min and cured at200° C. for 20 min. Each solution formed a cured brown polymer which washard and insoluble in water and solvents, and showed an excellentadhesion to glass.

Example 4

Examples 1-3 were repeated in the presence of 5% by weight ammoniumsulfate. The polymers became insoluble in water in less than 10 min.

Example 5

To 116 g HMDA dissolved in 214 g water was added slowly 98 g maleicanhydride (Man), this was a molar ratio of 1:1. The resulting solutionwas refluxed for 60 minutes to prepare an amino-amide oligomer. Thesolution was opaque with 50% solids. The solution was then used torepeat example 1 with the observed results being the same, i.e., thecured polymer was hard and insoluble in water and solvents, and showedexcellent adhesion to glass.

Example 6—Plant Trial

To examine the performance of the binder on an insulation batt, a bindersolution was prepared and applied in the manufacture of the insulationbatt. Processing and performance of the batts made with the binder ofthis invention was compared with the batts manufactured with apolyacrylic acid binder cured with triethanol amine.

To prepare the binder, 116 g HMDA was dissolved in 754 kg water. To thissolution was added 98 kg maleic anhydride with stirring until dissolved.To this solution was added 540 kg anhydrous dextrose. When the dextrosedissolved, 37.7 kg ammonium sulfate was added. After all the ingredientsdissolved, the clear binder solution was utilized in the manufacture ofR-19 and R-13 insulation batt.

The binder was applied at the rate of 4.5% binder on glass fibercontaining 1% (based on binder) of an amino-propyl silane coupling agentand about 0.5% dedusting oil. The batt was cured at 210° C. with an ovenresidence time of two minutes. The 32″ droop (sag) and recovery data forR-19 insulation batt products are presented in Table 1 and Table 2 belowrespectively:

TABLE 1 32″ Droop Data for R-19 Unaged 7 Day 14 Day Control (Acrylic)1.1 1.7 2.2 HP 1.0 1.3 1.6

TABLE 2 Recovery fir R-19 Unaged 7 Day 14 Day Control (Acrylic) 6.916.48 6.38 HP 6.85 6.55 6.41As seen from Table 1 and Table 2, the R-19 insulation product of the newformaldehyde free binder of this invention (HP) has better performancecompared to the commercial acrylic control.

The principles, preferred embodiments, and modes of operation of thepresent invention have been described in the foregoing specification.The invention which is intended to be protected herein, however, is notto be construed as limited to the particular forms disclosed, sincethese are to be regarded as illustrative rather than restrictive.Variations and changes may be made by those skilled in the art withoutdeparting from the spirit of the invention.

What is claimed is:
 1. A process of making a formaldehyde-freefiberglass product, wherein the process comprises: applying a bindercomposition to glass fibers, wherein the binder composition comprises:an aldehyde or ketone, and an amino-amide oligomer consisting of anaddition product of an amine and a carbonyl-containing compound; andcuring the binder composition while present on the glass fibers to makethe formaldehyde-free fiberglass product, wherein the cured bindercomposition includes reaction products of the aldehyde or ketone and theamino-amide oligomer.
 2. The process of claim 1, wherein the aldehyde orketone comprises a reducing sugar.
 3. The process of claim 2, whereinthe reducing sugar comprises dextrose.
 4. The process of claim 1,wherein the amine is a diamine having at least one primary amine group.5. The process of claim 1, wherein the amine comprises at least oneamine selected from the group consisting of 1,2-diethylamine,1,3-propanediamine, 1,4-butanediamine, 1,5-pentanediamine,1,6-hexanediamine, α, α′-diaminoxylene, diethylenetriamine,triethylenetetramine, and tetraethylenepentamine.
 6. The process ofclaim 1, wherein the carbonyl-containing compound is selected from thegroup consisting of a saturated or unsaturated anhydride, a carboxylicacid, an ester, and salts and mixtures thereof.
 7. The process of claim1, wherein the carbonyl-containing compound is selected from the groupconsisting of maleic acid, fumaric acid, maleic anhydride, mono- anddi-esters of maleic acid, mono- and di-esters of fumaric acid, andphthalic anhydride, tetrahydro phthalic anhydride, succinic acid andanhydride, glutaric acid and anhydride, salts and mixtures thereof. 8.The process of claim 1, wherein the carbonyl-containing compound ismaleic anhydride.
 9. The process of claim 1, wherein the bindercomposition further comprises at least one component selected from thegroup consisting of adhesion promoters, oxygen scavengers, moisturerepellants, solvents, emulsifiers, pigments, fillers, anti-migrationaids, coalescent aids, wetting agents, biocides, plasticizers,organosilanes, anti-foaming agents, colorants, waxes, suspending agents,anti-oxidants, and crosslinking catalysts.
 10. The process of claim 1,wherein the formaldehyde-free fiberglass product is building insulation.11. The process of claim 1, wherein the formaldehyde-free fiberglassproduct is a microglass-based substrate useful for any of a printedcircuit board, battery separator, filter stock, or reinforcement scrim.12. The process of claim 1, wherein the formaldehyde-free fiberglassproduct is a fiberglass substrate useful in a roofing membrane.
 13. Aprocess of making a formaldehyde-free fiberglass product, wherein theprocess comprises: reacting an amine and a carbonyl-containing compoundto form an amino-amide oligomer, mixing the amino-amide oligomer with areducing sugar to form a binder composition; applying the bindercomposition to glass fibers; and curing the binder composition whilepresent on the glass fibers to make the formaldehyde-free fiberglassproduct, wherein the cured binder composition includes reaction productsof the reducing sugar and the amino-amide oligomer.
 14. The process ofclaim 13, wherein the amino-amide compound is in an aqueous medium. 15.The process of claim 13, wherein the amine and the carbonyl-containingcompound are reacted at a temperature range of 120° C. to 150° C. 16.The process of claim 13, wherein the curing of the binder compositionoccurs at a temperature of 100° C. to 300° C.
 17. The process of claim13, wherein the binder composition is an aqueous solution.
 18. Theprocess of claim 13, wherein the amine comprises at least one amineselected from the group consisting of 1,2-diethylamine,1,3-propanediamine, 1,4-butanediamine, 1,5-pentanediamine,1,6-hexanediamine, α, α′-diaminoxylene, diethylenetriamine,triethylenetetramine, and tetraethylenepentamine.
 19. The process ofclaim 13, wherein the carbonyl-containing compound comprises at leastone compound selected from maleic acid, fumaric acid, maleic anhydride,mono- and di-esters of maleic acid, mono- and di-esters of fumaric acid,and phthalic anhydride, tetrahydro phthalic anhydride, succinic acid andanhydride, glutaric acid and anhydride, salts and mixtures thereof. 20.The process of claim 1, wherein the cured binder composition furthercomprises a polyamino-amide and a polyamino-imide.